Why Smart Leaders Know What to Change:

But Still Don't Do It

In this episode of Pivot Point Strategy For Change - I have a deeply honest conversation with executive coach Jen Wilson about why meaningful organizational change starts with the internal work most leaders avoid, and how trust inside teams is built through shared commitment, not strategic planningalone. We explore how trust is actually rebuilt during organizational disruption, and why so many leaders struggle to follow through even when they know exactly what needs to change. Jen breaks down the fears that derail decision-making: fear of failure, fear of visibility, and those relentless 3 a.m. thoughts that surface when the pressureof leadership feels overwhelming.

We also examine how seemingly practical structures like meeting formats either strengthen trust or quietlyerode it, and why alignment with core values is essential for sustainable growth. Jen shares her own pivot point—that moment she returned home late one night, exhausted and empty despite her professional success, realizing her lifewas completely misaligned with her true values.

This conversation digs into how to recognize the signs of misalignment before they become a crisis, how to listento your intuition (especially for women in leadership), and how to take practical steps toward realignment without needing a dramatic breakdown to justify the change. Jen emphasizes that transformation doesn't require drastic action. Instead, she advocates for small, incremental shifts that can lead tosignificant change—like her experience of simply visiting a different coffee shop, which opened her eyes to her own preferences and desires.

We talk about navigating change without burning out, scaling organizations without losing yourself, and making meaningful personal and professional shifts when you're standing at acrossroads. Jen also addresses how leadership must evolve to meet the expectations of Gen Z and the generations that follow, and why creating a common language makes honest, courageous conversations possible within teams.

This episode is for executives, entrepreneurs, therapists, coaches, and anyone who feels quietly misaligned,sensing that something needs to change but unsure where to start. Jen offers a free values workbook to help you clarify what you truly stand for, and we discuss the questions that reveal whether you're living in accordance with yourcore values: "What do I know to be true right now?" and "Am Iliving according to what matters most?"

The journey of transformation begins with recognizing the need for change and being willing to embrace discomfort. This conversation reminds us that listening to our intuition andaligning our actions with our values are essential steps toward personal and professional fulfillment. By asking the right questions and taking small steps, we can navigate our own pivot points and create a more authentic, satisfyinglife.

In this conversation, I sit down with Jen Wilson to explore how trust is rebuilt inside teams and why real organizational change always starts with the internal work we’re often tempted to avoid. We talk about what actually makes teams function well—being aligned around a shared outcome, doing the deeper personal and collective work, and creating a common language that allows for honest, courageous conversations. Jen also shares how practical structures, like how meetings are truly used, can either support or undermine trust and effectiveness.We then dig into a question I see come up again and again with leaders: why so many people understand what needs to change but struggle to follow through. Jen offers a powerful perspective on the fears that quietly get in the way, including the fear of failure, the fear of being seen, and the late-night “3 a.m. thoughts” that surface when the pressure of leadership feels overwhelming. This episode is for leaders and teams who want to build trust, improve team dynamics, and lead with greater clarity, self-awareness, and courage.

In my recent conversation with Michal LeBaron, Iwas struck by how her story embodies what I call a pivot point—that moment when a person takes radical ownership of their healing. Michal shared that her journey began in an unexpected way: a quiet decision, made whilesitting in her recliner, to simply say to herself, “I am choosing toheal.” It wasn’t dramatic, but it was powerful. That inner commitment became the turning point that changed everything for her. Before that moment, she described feeling defeated and even betrayed by her body. For years, she’d been locked in a battle with symptoms that seemed to signal breakdown rather than communication. But as we spoke,Michal reflected on how learning to interpret those signals differently transformed her experience. Once she began to view her body as a messenger instead of an enemy, everything softened. Her symptoms becamefeedback—information guiding her toward balance rather than proof of failure. As she put it, her body became “a partner, a friend, a teacher.”

A central part of our discussion focused on the nervoussystem and its profound role in healing. Michal realized that her challenges weren’t just about external triggers like food or environment—they were rooted in an overworked regulatory system. The body, she explained, hadbeen doing its best to keep her safe, even when it looked like it was breakingdown. By tending to her nervous system, she discovered a more empowered way toapproach her well-being—one built on trust, not control.

We also talked about the mindset shift that made thishealing possible. Michal described moving from a place of frustration andself-blame to one of compassion and curiosity. She began to ask herself, “Howam I caring for myself through this? Do I truly support myself when things gethard?” That self-inquiry opened a door to deeper self-nurturing,turning her inner dialogue into a practice of partnership rather than punishment.

As our interview closed, Michal spoke about gratitude—anemotion she never expected to feel toward the challenges that had once caused her so much suffering. She now sees her symptoms as allies, guiding her to realign with health, awareness, and authenticity. At one point she wonderedaloud, “What happens when I no longer need my symptoms to alert me?” It was such a powerful reflection—one that stayed with me long after our conversation ended.

Michal’s story is a beautiful reminder that healing oftenbegins not with a treatment or diagnosis, but with a decision. It’s the quiet pivot from fear to trust, from resistance to listening. Her journey shows that the body, when approached with respect and curiosity, has a remarkable way ofguiding us back to ourselves.